Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase

Molecular recognition based on chirality has fundamental importance in many biological processes. Deuterium quadrupole splittings from the aromatic ring and mesophase components of two series of optical isomers, L- and D-N-acyl-1-phenyl-d5-2-aminopropanes, dissolved in anionic nematic cholesteric ly...

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Autores principales:	AHUMADA,HERNÁN, MONTECINOS,RODRIGO, ALEGRÍA,SERGIO, ARAYA-MATURANA,RAMIRO, WEISS-LÓPEZ,BORIS E
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2005
Materias:	2H-NMR Quadrupole Splittings Order Parameters Chiral Discrimination
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000100010
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spelling	oai:scielo:S0717-970720050001000102005-05-27Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic LyomesophaseAHUMADA,HERNÁNMONTECINOS,RODRIGOALEGRÍA,SERGIOARAYA-MATURANA,RAMIROWEISS-LÓPEZ,BORIS E 2H-NMR Quadrupole Splittings Order Parameters Chiral Discrimination Molecular recognition based on chirality has fundamental importance in many biological processes. Deuterium quadrupole splittings from the aromatic ring and mesophase components of two series of optical isomers, L- and D-N-acyl-1-phenyl-d5-2-aminopropanes, dissolved in anionic nematic cholesteric lyotropic liquid crystals of cesium N-dodecanoyl-L-threoninate, were measured using²H-NMR. The length of the acyl chain was 1, 2, 3, 4, 5, 7 and 10 carbon atoms. The two order parameters that fully characterize the average alignment of the aromatic ring were calculated. Both the L- and D- isomers are strongly attached to the aggregate. L-C1, D-C1, L-C2 and D-C2 derivatives have the same order parameters which suggests that are located in the same region of the interface, possibly H-bonded to the interstitial water molecules with the NH and/or CO groups. Increasing the hydrophobic chain length by one carbon atom decreases the overall alignment of the ring and differences between L-C3 and D-C3 were observed. Molecules with longer acyl chain progressively increase their quadrupole splittings, suggesting an increase in alignment. Increasing differences in the order parameter of the symmetry axis of the aromatic rings in both isomers were observed from C3 to C5, and almost no differentiation is detected between L-C7 and D-C7. However, differentiation appears again for C10, and is attributable to interactions with a second chiral center of the head groupinfo:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.50 n.1 20052005-03-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000100010en10.4067/S0717-97072005000100010
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	2H-NMR Quadrupole Splittings Order Parameters Chiral Discrimination
spellingShingle	2H-NMR Quadrupole Splittings Order Parameters Chiral Discrimination AHUMADA,HERNÁN MONTECINOS,RODRIGO ALEGRÍA,SERGIO ARAYA-MATURANA,RAMIRO WEISS-LÓPEZ,BORIS E Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
description	Molecular recognition based on chirality has fundamental importance in many biological processes. Deuterium quadrupole splittings from the aromatic ring and mesophase components of two series of optical isomers, L- and D-N-acyl-1-phenyl-d5-2-aminopropanes, dissolved in anionic nematic cholesteric lyotropic liquid crystals of cesium N-dodecanoyl-L-threoninate, were measured using²H-NMR. The length of the acyl chain was 1, 2, 3, 4, 5, 7 and 10 carbon atoms. The two order parameters that fully characterize the average alignment of the aromatic ring were calculated. Both the L- and D- isomers are strongly attached to the aggregate. L-C1, D-C1, L-C2 and D-C2 derivatives have the same order parameters which suggests that are located in the same region of the interface, possibly H-bonded to the interstitial water molecules with the NH and/or CO groups. Increasing the hydrophobic chain length by one carbon atom decreases the overall alignment of the ring and differences between L-C3 and D-C3 were observed. Molecules with longer acyl chain progressively increase their quadrupole splittings, suggesting an increase in alignment. Increasing differences in the order parameter of the symmetry axis of the aromatic rings in both isomers were observed from C3 to C5, and almost no differentiation is detected between L-C7 and D-C7. However, differentiation appears again for C10, and is attributable to interactions with a second chiral center of the head group
author	AHUMADA,HERNÁN MONTECINOS,RODRIGO ALEGRÍA,SERGIO ARAYA-MATURANA,RAMIRO WEISS-LÓPEZ,BORIS E
author_facet	AHUMADA,HERNÁN MONTECINOS,RODRIGO ALEGRÍA,SERGIO ARAYA-MATURANA,RAMIRO WEISS-LÓPEZ,BORIS E
author_sort	AHUMADA,HERNÁN
title	Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
title_short	Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
title_full	Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
title_fullStr	Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
title_full_unstemmed	Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase
title_sort	chiral discrimination of l- and d-n-acyl-1-phenyl-d5-2-aminopropanes in a cesium n-dodecanoyl-l-threoninate cholesteric nematic lyomesophase
publisher	Sociedad Chilena de Química
publishDate	2005
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000100010
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Chiral Discrimination of L- and D-N-acyl-1-phenyl-d5-2-aminopropanes in a Cesium N-Dodecanoyl-L-Threoninate Cholesteric Nematic Lyomesophase

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